Questions tagged [inductive-effect]
Use for questions regarding the so called inductive effect of substituents on properties of compounds.
80
questions
0
votes
1
answer
154
views
Can alkyl groups show -I effect?
Inductive effect is the partial shifting of the sigma-bonding electrons towards more EN (take as electronegativity or electronegative in this text) atom so why we will say that alkyl groups will ...
- 89
1
vote
1
answer
134
views
Is there a quantitative definition of inductive effect?
Usually, Inductive effects are compared using the electronegativities and distances. However, this only works in compounds with similar structures. For example, we can predict the following orders of ...
- 2,205
-3
votes
1
answer
71
views
+M or -I for chlorine? Major product in free radical chlorination and bromination of 2-chloropropane?
Is the +M or -I effect more dominant in when an alkyl (mono)halide is subject to free radical chlorination/bromination?
For example what will be the major product in case of free radical (mono)...
- 89
-1
votes
1
answer
165
views
Why is the melting point of 4-bromoacetanilide so high? Does it have any reason to do with the chemical structure, or the para aspect?
We used melting point to determine the type of bromoacetanilide, and it was closest to 4-bromoacetanilide. How can I explain why the melting point was what it is?
4
votes
2
answers
401
views
Acidic strength of nitrophenols
I've seen the pKa values of Nitrophenol as follows:-
pKa of o-nitrophenol= 7.23
pKa of p-nitrohenol= 7.14
so p-nitrophenol is more acidic than p-nitrophenol
But both phenoxide ions are stabilized ...
- 144
-2
votes
1
answer
70
views
Acidic strength order among hydroxytetralones [closed]
I can understand in 1 the conjugate base has more stability for better resonance but in 2 and 3 the effect of resonance cannot be considered. How can we compare the inductive effect in such case?
1
vote
1
answer
346
views
Why is the inductive effect possible?
Firstly, I must preface that I am a Biology student. To elaborate my question, I was looking for the reason why carboxylic acids are more acidic than alcohols, despite both compounds containing —OH ...
- 67
2
votes
1
answer
1k
views
Is NH2 electron donating or electron withdrawing? [closed]
Can anyone explain why NH2 shows -I in inductive effect and +R in resonance effect? I mean NH2 is ready to take electrons in inductive effect (with its electronegativity) but in the resonance effect, ...
- 31
3
votes
0
answers
86
views
Is Bent's Rule an alternative explanation for the Inductive Effect?
Today I read that Bent's Rule can be used to explain the inductive effect (I was reading the Consequences section of this Wikipedia article). If I understand it correctly, for a molecule CL3R, the ...
- 325
1
vote
0
answers
157
views
Effect of beta branching and carbocation rearrangement on SN1 reaction rates
My book (NCERT class 12 Chemistry) asks
Predict the order of reactivity of the four isomeric bromobutanes in SN1 and SN2 reactions.
The answer given for SN1 is
1-bromobutane < 1-bromo-2-...
- 11
3
votes
0
answers
261
views
How to establish trend of carboxylic acid acidity in the presence of certain substituents?
I encountered a question in my textbook which asked the following:
At first, i thought that i can approach it in the same way i sort the effect of EDG and EWG on the acidity of phenols, that is, ...
- 107
0
votes
0
answers
2k
views
What is the correct order of Relative Inductive Effect (-I) of different groups?
This confusion has put me in problem several times since last 2 years and I have been looking for a clarification but it seems that answer depends upon who you ask. I have several examples where I ...
- 149
1
vote
1
answer
964
views
Effect of electron-donating and electron-withdrawing groups on the C=O bond
My notes states this:
An electronegative element tends to draw in the electrons between the carbon and oxygen atoms through its electron-withdrawing effect. This strengthens the C=O bond.
An electron-...
- 67
1
vote
0
answers
81
views
Comparing acidic strength of acetic and p-anisic acids
In p-anisic acid the phenyl ring with methoxy group acts as strong electron donating group by mesomeric effect (+M), whereas in acetic acid there is only an electron donating nature by inductive ...
- 156
-1
votes
1
answer
89
views
Reactivity of Alkenes with HBr [closed]
I am new in the Organic Chemistry (World of Reactions). I had got one question in my test. But, when I had seen it, I got no proper logic to tick the correct answer, and then when I saw solution, then ...
0
votes
1
answer
1k
views
Inductive Effect of -CH3 group [duplicate]
3° carbocations are the most stable because of the +I effect of -CH3 group. This group gives a slight negative charge to the central carbon atom, which makes it less positively charged and thus, more ...
user119416
1
vote
0
answers
539
views
Does inductive effect operate through pi bonds?
I have been told that the inductive effect is only present in sigma bonds by my teacher, and the book I've referenced also says the same thing.
However, I can't think of why this is. Answers to this ...
- 333
0
votes
0
answers
192
views
Why does chlorine show a mesomeric effect in haloarenes and an inductive effect in haloalkanes?
Chlorine shows the +R effect in haloarenes and the -I effect in haloalkanes. Does chlorine do the same for all cyclic compounds or only for aromatic rings? Is this just another experimentally seen ...
- 32
2
votes
0
answers
427
views
Difference between nucleophilicity of phenoxide ion and acetate anion in protic/aprotic solvent
As far as I could think, the phenoxide ion is comparatively larger as compared to acetate ion, so it should undergo less solvation in presence of a protic solvent and thus its nucleophilicty should be ...
- 89
1
vote
0
answers
26
views
Ortho effect and the relative acidity in aromatic acids [duplicate]
What is the order of the acidity of 2-methyl benzoic acid and 2-isopropyl benzoic acid?
I know about ortho effect which states that the acidity of ortho- substituted aromatic carboxylic acids is ...
1
vote
1
answer
2k
views
How come the methyl group (-CH3) is electron donating?
If the inductive effect operates purely through electronegativity differences, how come the methyl group is considered to donate electrons through the inductive effect? My textbook says that there is ...
- 11
0
votes
0
answers
320
views
Why is the carbanion stability order the way it is? (3*<2*<1*)
According to the lecture notes I made, a 1* carbanion is more stable than a 3* carbanion. I can't grasp exactly why. (I had a look at the similar questions, the answers didn't help)
With my very ...
- 11
2
votes
0
answers
82
views
Hydrogen as a reference in inductive effect
What does it mean when we say that I-effect of hydrogen is taken as zero ?
I think that it means that partial displacement of sigma bond electrons between two atoms of different electronegativity is ...
user108965
4
votes
1
answer
243
views
Why don't we consider the attached hydrogens in inductive effect?
Consider the molecule 1-chloroethane
Let carbon attached to $\ce{Cl}$ be $\ce{C1}$ and other one be $\ce{C2}$. While learning inductive effect I was told that $\ce{Cl}$ due to high electronegativity ...
user108965
2
votes
1
answer
607
views
Why is ethanol more acidic than acetone?
The acidity of a compound is determined by the stability of its conjugate base and the major structure of enolate has a negative charge on the Oxygen atom. Moreover, the negative charge on the O-atom ...
- 442
2
votes
1
answer
490
views
Effect of distance on the mesomeric effect
I have always thought that mesomeric effect is somewhat dependent on distance.
But I recently came across a question where I was asked to predict the order of stability of o-methoxyphenyl carbocation ...
12
votes
2
answers
1k
views
Why hydrogen bonding in some acids make them a stronger acid when it is present even before deprotonation?
If we take the example of salicylic acid, hydrogen bonding is present in the acid as follows:
Even after deprotonation, it has intramolecular hydrogen bonding as follows:
My question:
p-...
- 442
3
votes
1
answer
539
views
Stability of meta ethyl and meta methyl benzene carbocations respectively
It is known that Methyl has a greater +I effect than Ethyl, but here, in this case, the condition is satisfied in the para benzene carbocations whereas, in the meta forms, it is the opposite. Shouldn'...
- 39
1
vote
1
answer
100
views
Carbocation formation and stability from bromo compounds
When heated,the following bromo-species all form carbocations via $\sigma$ bond cleavage. For each structure draw the corresponding carbocation and briefly describe how it is stabilised.
This is my ...
- 29
0
votes
0
answers
47
views
Comparing nucleophilic strengths of tetrahydropyran and (2R,6R)-2,6 dimethyltetrahydropyran
Compare the nucleophilic strengths of the following two compounds:
According to me it should be the second one, that is, (2R,6R)-2,6-dimethyltetrahydropyran because the methyl groups would exert +I ...
- 1,251
8
votes
2
answers
325
views
How do steric effects affect inductive effect in compounds with tetravalent nitrogen?
I want to compare the electron density on methyl group between tri‐tert‐butyl(methyl)azanium (1) and triisopropyl(methyl)azanium (2), i.e. essentially the inductive effects of $\ce{-\overset{+}{N}R3}$ ...
- 1,409
1
vote
0
answers
52
views
Evaluating inductive effects in cyclic compounds
I was required to find the products on heating the hydroxide of;
Now it's easy enough to find the answer; Hoffman elimination isn't going to happen from the methyl, and the n-propyl doesn't have $\...
- 1,116
0
votes
1
answer
1k
views
Acidic nature comparison; benzoic acid and phenylacetic acid
The $\ce{pK_a}$ values of benzoic acid and phenylacetic acid are around 4.2 and 4.31 respectively.
In benzoic acid, you have the resonance being the dominating effect, destabilizing a conjugate base ...
- 1,116
4
votes
2
answers
275
views
What does acidity of para-alkyl substituted phenols depend on?
Problem
Arrange the following organic compounds in decreasing order of acidity.
Answer
Question
According to my knowledge the answer should be P, Q, R, S. As we proceed from P to S we are ...
- 151
3
votes
1
answer
147
views
Stabilization of multiple bonds through inductive effects
In the conversion of m-chloroanisole to m-anisidine using $\ce{NaNH2}$ and liquid $\ce{NH3}$, apparently the reason the $\ce{NH2-}$ goes for the meta- position instead of the para position is that, in ...
- 1,116
2
votes
0
answers
153
views
Why does the carboxylate ion show positive inductive effect?
While solving some problems on general organic chemistry, I came across this question that asked for the nature of inductive effects of $\ce{-CH_3}, \ce{-CO_2^-}, \ce{-Br}, \ce{-NH_3^+}$.
And in the ...
- 466
-3
votes
1
answer
134
views
Confusion in comparing the contribution of resonating structures to resonance hybrid [closed]
So I was comparing the $+M$ effect of $\ce{-CH^-_2}$, $\ce{-NH^-}$ and $\ce{-O^-}$. Answer was given as:
$$ \ce{-CH^-2 > -NH^- > -O^-}$$
So, I attach them with ethene and made their respective ...
- 304
3
votes
1
answer
149
views
Relative acidity of acetic acid derivatives with strongly withdrawing substituents
What would be the order of $\mathrm{p}K_\mathrm{a}$ values of the following:
$\ce{O2N-CH2-CO2H},$
$\ce{Me3\overset{+}{N}-CH2-CO2H},$
$\ce{NC-CH2-CO2H},$
$\ce{HO-CH2-CO2H}?$
Since only the groups ...
- 1,208
0
votes
0
answers
74
views
Combined Effect of Steric Inhibition of Resonance and Inductive Effect
While qualitatively comparing the acidic nature of o-methyl benzoic acid and benzoic acid, we consider the steric effect due to which the $\ce{-COOH}$ group loses its planarity and the +M effect of $\...
- 11
1
vote
1
answer
271
views
How to explain regioselectivity in nucleophilic aromatic substitution
I’m trying to rationalise the major regioisomeric product of the following reaction of an arylchloride in the presence of sodium amide:
I have predicted that the para-substituted product is formed as ...
- 49
2
votes
1
answer
136
views
Order of −I effect among ethenyl and 1-propenyl groups
We know that both ethenyl $\ce{-CH=CH}_2$ and 1-propenyl $\ce{-CH=CH-CH3}$ are electron-withdrawing groups when attached to hydrocarbon chain. Which one has greater electron withdrawing power?
The $\...
- 129
1
vote
1
answer
652
views
Does the benzene ring in styrene show a negative inductive effect on the ethenyl group?
I know that a group exerts an inductive effect on another one if there is a difference in electronegativity. In the case of styrene (1) all the atoms are sp2-hybridized. So, how could the phenyl ring ...
- 59
0
votes
1
answer
382
views
Estimation of dipole moments in aromatic compounds
If it asks to compare dipole moment in aromatic compounds then do we see inductive or resonance effects or do we see a mix of both?
E.g. we have to compare dipole moment in pyrrole and furan then in ...
- 294
-1
votes
1
answer
997
views
Comparing reactivity of 1-chloroethane and 1-chloropropane in an SN1 reaction
Beginning with a reference to a well known question.
Order by reactivity towards SN1 reaction.
According to some facts about SN1 reactions, rate depends on:
Stability of carbocations
Better leaving ...
user98209
0
votes
0
answers
298
views
Inductive effect of acetyl group
Question:
Since the acetyl group provides $-M$, methyl $+I$ and chlorine $-I$, it is obvious that the correct order is as given in option $(a)$
However while solving such questions I would compare ...
- 264
0
votes
0
answers
279
views
Does the electron displacement effect act only on sigma electrons?
Our teacher told us that the inductive effect or the electron displacement effect can only affect the sigma electrons. I did not understand why this should be.
I reasoned it can not affect the pi ...
- 183
0
votes
1
answer
607
views
Carbanion Stability order [duplicate]
Why is a 3° Carbanion unstable than 1° Carbanion? Carbon atom with negative charge will become little electropositive relative to a neutral carbon. So if a Carbanion is attached to three neutral ...
1
vote
1
answer
549
views
The most acidic hydrogen among ethane, ethene, ethyne and allene
Among
$$\ce{CH3-CH3}\qquad\ce{CH2=CH2}\qquad\ce{HC≡CH}\qquad\ce{CH2=C=CH2}$$
I need to find out the one having highest acidic hydrogen.
As per my observations, there are two equivalent resonating ...
- 297
3
votes
1
answer
3k
views
Ortho-para directing and meta directing groups: Activating or deactivating the aromatic ring?
Determine the reactivity of the above compounds (activating or deactivating; ortho-para or meta directing). Explain your answers. You may use resonance structures in your explanation. Which molecule ...
- 143
4
votes
2
answers
4k
views
Does Cl- Have more -I effect or +M effect ( Resonance effect)?
In this question my answer was (A) because I thought $\ce{NH2}$ group would give more electrons than $\ce{Cl-}$. But the correct answer is (D) and my teacher's reason is that chlorine has more ...
- 63